# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'B. Kariuki' _publ_contact_author_email KariukiB@cardiff.ac.uk loop_ _publ_author_name M.Elliott B.Kariuki S.Raw C.Morton N.Hewitt N.Bennett S.Tomasi data_mce1101b _database_code_depnum_ccdc_archive 'CCDC 854352' #TrackingRef 'mce1101b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O6' _chemical_formula_sum 'C18 H20 N2 O6' _chemical_formula_weight 360.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.6377(3) _cell_length_b 7.8225(3) _cell_length_c 32.1299(10) _cell_angle_alpha 93.748(2) _cell_angle_beta 91.221(2) _cell_angle_gamma 109.094(2) _cell_volume 1808.28(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4574 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 26.39 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9705 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8271 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 26.39 _reflns_number_total 6414 _reflns_number_gt 4574 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997' _computing_structure_solution 'Sir-92 (A. Altomare et al., 1992)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-99 for Windows (Farrugia, 1995)' _computing_publication_material 'WinGX publication routines (Farrugia, 1995)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+2.0323P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.037(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6414 _refine_ls_number_parameters 476 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1050 _refine_ls_R_factor_gt 0.0706 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3771(4) 0.3548(4) 0.19520(9) 0.0266(6) Uani 1 1 d . . . C2 C 0.3785(4) 0.5187(4) 0.22238(9) 0.0274(6) Uani 1 1 d . . . C3 C 0.4049(4) 0.6877(4) 0.20703(9) 0.0271(6) Uani 1 1 d . . . C4 C 0.3818(4) 0.8320(4) 0.23074(9) 0.0300(7) Uani 1 1 d . . . H4 H 0.3974 0.9454 0.2196 0.036 Uiso 1 1 calc R . . C5 C 0.3347(4) 0.8019(4) 0.27154(9) 0.0302(7) Uani 1 1 d . . . C6 C 0.3156(4) 0.6412(4) 0.28931(9) 0.0312(7) Uani 1 1 d . . . H6 H 0.2891 0.6285 0.3179 0.037 Uiso 1 1 calc R . . C7 C 0.3362(4) 0.4984(4) 0.26404(9) 0.0296(7) Uani 1 1 d . . . H7 H 0.3212 0.3856 0.2754 0.036 Uiso 1 1 calc R . . C8 C 0.2501(4) 0.1841(4) 0.13174(9) 0.0293(7) Uani 1 1 d . . . H8A H 0.2131 0.0637 0.1433 0.035 Uiso 1 1 calc R . . H8B H 0.3759 0.2098 0.1210 0.035 Uiso 1 1 calc R . . C9 C 0.1129(4) 0.1852(4) 0.09669(9) 0.0295(7) Uani 1 1 d . . . C10 C 0.1587(4) 0.3734(4) 0.08190(9) 0.0321(7) Uani 1 1 d . . . H10 H 0.2815 0.4316 0.0738 0.038 Uiso 1 1 calc R . . C11 C 0.0395(4) 0.4623(4) 0.07951(9) 0.0343(7) Uani 1 1 d . . . H11 H 0.0835 0.5810 0.0701 0.041 Uiso 1 1 calc R . . C12 C -0.1598(4) 0.3913(4) 0.09042(9) 0.0330(7) Uani 1 1 d . . . H12 H -0.1777 0.4766 0.1132 0.040 Uiso 1 1 calc R . . C13 C -0.2015(4) 0.2093(4) 0.10787(9) 0.0341(7) Uani 1 1 d . . . H13 H -0.3223 0.1548 0.1176 0.041 Uiso 1 1 calc R . . C14 C -0.0830(4) 0.1195(4) 0.11077(9) 0.0326(7) Uani 1 1 d . . . H14 H -0.1243 0.0056 0.1226 0.039 Uiso 1 1 calc R . . C15 C 0.1346(5) 0.0520(5) 0.06119(10) 0.0440(8) Uani 1 1 d . . . H15A H 0.0436 0.0415 0.0384 0.066 Uiso 1 1 calc R . . H15B H 0.1138 -0.0675 0.0718 0.066 Uiso 1 1 calc R . . H15C H 0.2600 0.0972 0.0509 0.066 Uiso 1 1 calc R . . C16 C -0.2959(4) 0.3871(5) 0.05375(9) 0.0363(7) Uani 1 1 d . . . H16 H -0.4241 0.3381 0.0640 0.044 Uiso 1 1 calc R . . C17 C -0.2834(5) 0.2612(5) 0.01675(10) 0.0484(9) Uani 1 1 d . . . H17A H -0.1577 0.3023 0.0064 0.073 Uiso 1 1 calc R . . H17B H -0.3726 0.2623 -0.0055 0.073 Uiso 1 1 calc R . . H17C H -0.3119 0.1376 0.0254 0.073 Uiso 1 1 calc R . . C18 C -0.2703(5) 0.5785(5) 0.04074(11) 0.0456(9) Uani 1 1 d . . . H18A H -0.2790 0.6564 0.0652 0.068 Uiso 1 1 calc R . . H18B H -0.3673 0.5731 0.0197 0.068 Uiso 1 1 calc R . . H18C H -0.1483 0.6284 0.0290 0.068 Uiso 1 1 calc R . . C19 C 0.8217(4) 1.1834(4) 0.30108(9) 0.0299(7) Uani 1 1 d . . . C20 C 0.8325(4) 1.3322(4) 0.27284(9) 0.0270(6) Uani 1 1 d . . . C21 C 0.8072(4) 1.4947(4) 0.28700(9) 0.0297(7) Uani 1 1 d . . . C22 C 0.8360(4) 1.6385(4) 0.26223(9) 0.0304(7) Uani 1 1 d . . . H22 H 0.8171 1.7483 0.2719 0.036 Uiso 1 1 calc R . . C23 C 0.8939(4) 1.6134(4) 0.22242(9) 0.0294(7) Uani 1 1 d . . . C24 C 0.9179(4) 1.4553(4) 0.20683(9) 0.0291(7) Uani 1 1 d . . . H24 H 0.9558 1.4430 0.1791 0.035 Uiso 1 1 calc R . . C26 C 0.9341(5) 1.1207(4) 0.36568(9) 0.0355(7) Uani 1 1 d . . . H26A H 0.9925 1.0331 0.3541 0.043 Uiso 1 1 calc R . . H26B H 0.8066 1.0526 0.3733 0.043 Uiso 1 1 calc R . . C27 C 1.0476(4) 1.2317(4) 0.40407(9) 0.0334(7) Uani 1 1 d . . . C28 C 1.2390(4) 1.3389(4) 0.39116(9) 0.0334(7) Uani 1 1 d . . . H28 H 1.3114 1.2737 0.3783 0.040 Uiso 1 1 calc R . . C29 C 1.3126(4) 1.5179(4) 0.39658(9) 0.0329(7) Uani 1 1 d . . . H29 H 1.4339 1.5726 0.3871 0.040 Uiso 1 1 calc R . . C30 C 1.2174(4) 1.6402(4) 0.41662(9) 0.0322(7) Uani 1 1 d . . . H30 H 1.2035 1.7225 0.3952 0.039 Uiso 1 1 calc R . . C31 C 1.0261(5) 1.5338(5) 0.42868(10) 0.0379(8) Uani 1 1 d . . . H31 H 0.9531 1.5988 0.4413 0.045 Uiso 1 1 calc R . . C32 C 0.9523(5) 1.3549(5) 0.42290(10) 0.0390(8) Uani 1 1 d . . . H32 H 0.8292 1.3010 0.4314 0.047 Uiso 1 1 calc R . . C33 C 1.0625(5) 1.0936(5) 0.43479(11) 0.0474(9) Uani 1 1 d . . . H33A H 1.1235 1.0131 0.4215 0.071 Uiso 1 1 calc R . . H33B H 0.9380 1.0215 0.4425 0.071 Uiso 1 1 calc R . . H33C H 1.1355 1.1581 0.4599 0.071 Uiso 1 1 calc R . . C34 C 1.3340(5) 1.7617(5) 0.45399(10) 0.0391(8) Uani 1 1 d . . . H34 H 1.2571 1.8293 0.4677 0.047 Uiso 1 1 calc R . . C35 C 1.3825(6) 1.6482(5) 0.48627(10) 0.0532(10) Uani 1 1 d . . . H35A H 1.2688 1.5566 0.4943 0.080 Uiso 1 1 calc R . . H35B H 1.4439 1.7270 0.5110 0.080 Uiso 1 1 calc R . . H35C H 1.4659 1.5879 0.4743 0.080 Uiso 1 1 calc R . . C36 C 1.5089(5) 1.9012(5) 0.43944(12) 0.0574(10) Uani 1 1 d . . . H36A H 1.5872 1.8384 0.4261 0.086 Uiso 1 1 calc R . . H36B H 1.5775 1.9797 0.4635 0.086 Uiso 1 1 calc R . . H36C H 1.4742 1.9751 0.4194 0.086 Uiso 1 1 calc R . . C25 C 0.8852(4) 1.3140(4) 0.23271(9) 0.0303(7) Uani 1 1 d . . . H25 H 0.8995 1.2029 0.2225 0.036 Uiso 1 1 calc R . . N1 N 0.4686(4) 0.7197(4) 0.16439(8) 0.0327(6) Uani 1 1 d . . . N2 N 0.3020(4) 0.9493(4) 0.29780(9) 0.0406(7) Uani 1 1 d . . . N3 N 0.7377(4) 1.5141(4) 0.32878(8) 0.0391(7) Uani 1 1 d . . . N4 N 0.9328(4) 1.7664(4) 0.19538(8) 0.0362(6) Uani 1 1 d . . . O1 O 0.2496(3) 0.3231(3) 0.16405(6) 0.0297(5) Uani 1 1 d . . . O2 O 0.4731(3) 0.2641(3) 0.20186(7) 0.0368(5) Uani 1 1 d . . . O3 O 0.5584(3) 0.6278(3) 0.14948(7) 0.0404(6) Uani 1 1 d . . . O4 O 0.4310(4) 0.8368(3) 0.14640(7) 0.0470(6) Uani 1 1 d . . . O5 O 0.2605(5) 1.0648(4) 0.27952(8) 0.0649(8) Uani 1 1 d . . . O6 O 0.3098(4) 0.9456(3) 0.33536(7) 0.0571(7) Uani 1 1 d . . . O7 O 0.9302(3) 1.2496(3) 0.33508(6) 0.0330(5) Uani 1 1 d . . . O8 O 0.7348(3) 1.0253(3) 0.29225(7) 0.0409(6) Uani 1 1 d . . . O9 O 0.6266(3) 1.3798(4) 0.34182(8) 0.0500(7) Uani 1 1 d . . . O10 O 0.7907(4) 1.6645(3) 0.34754(8) 0.0613(8) Uani 1 1 d . . . O11 O 1.0077(3) 1.7547(3) 0.16288(7) 0.0436(6) Uani 1 1 d . . . O12 O 0.8839(4) 1.8950(3) 0.20728(8) 0.0622(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0217(14) 0.0284(16) 0.0289(14) 0.0055(12) -0.0008(12) 0.0066(13) C2 0.0209(15) 0.0271(16) 0.0343(15) 0.0004(12) -0.0040(12) 0.0086(13) C3 0.0200(14) 0.0309(17) 0.0300(14) 0.0045(12) -0.0002(12) 0.0075(13) C4 0.0281(16) 0.0242(16) 0.0378(16) 0.0029(13) -0.0019(13) 0.0087(13) C5 0.0268(16) 0.0272(16) 0.0354(16) -0.0025(13) 0.0005(13) 0.0080(13) C6 0.0305(17) 0.0346(18) 0.0276(14) 0.0029(13) -0.0023(13) 0.0097(14) C7 0.0262(16) 0.0280(17) 0.0347(15) 0.0076(13) -0.0003(13) 0.0080(13) C8 0.0306(16) 0.0278(16) 0.0325(15) -0.0017(12) 0.0034(13) 0.0143(14) C9 0.0284(16) 0.0287(17) 0.0308(15) -0.0002(12) 0.0001(13) 0.0091(14) C10 0.0219(15) 0.0401(19) 0.0328(15) 0.0066(13) 0.0016(13) 0.0078(14) C11 0.0285(16) 0.0338(18) 0.0377(16) 0.0064(13) -0.0043(14) 0.0061(14) C12 0.0333(17) 0.0395(19) 0.0301(15) 0.0070(13) 0.0018(13) 0.0167(15) C13 0.0260(16) 0.043(2) 0.0321(15) 0.0086(13) 0.0053(13) 0.0086(15) C14 0.0306(17) 0.0308(17) 0.0339(16) 0.0064(13) -0.0009(13) 0.0062(14) C15 0.044(2) 0.048(2) 0.0387(18) -0.0099(15) 0.0002(16) 0.0165(17) C16 0.0280(17) 0.046(2) 0.0358(16) 0.0077(14) 0.0005(14) 0.0122(15) C17 0.044(2) 0.056(2) 0.0413(18) 0.0002(16) -0.0106(16) 0.0130(19) C18 0.0382(19) 0.052(2) 0.051(2) 0.0118(17) -0.0084(16) 0.0203(18) C19 0.0251(15) 0.0285(17) 0.0368(16) 0.0050(13) 0.0042(13) 0.0091(14) C20 0.0191(14) 0.0263(16) 0.0347(15) 0.0024(12) -0.0013(12) 0.0065(12) C21 0.0248(15) 0.0301(17) 0.0338(15) 0.0013(13) 0.0040(13) 0.0087(13) C22 0.0267(16) 0.0248(16) 0.0414(17) 0.0012(13) -0.0016(13) 0.0114(13) C23 0.0250(15) 0.0275(16) 0.0356(16) 0.0060(13) -0.0016(13) 0.0078(13) C24 0.0251(15) 0.0335(17) 0.0291(14) 0.0013(12) 0.0006(12) 0.0105(14) C26 0.0397(19) 0.0291(17) 0.0383(16) 0.0100(13) 0.0000(14) 0.0106(15) C27 0.0371(18) 0.0272(17) 0.0357(16) 0.0049(13) 0.0031(14) 0.0096(14) C28 0.0327(17) 0.0381(19) 0.0321(15) -0.0002(13) 0.0049(13) 0.0155(15) C29 0.0321(17) 0.0362(19) 0.0305(15) 0.0025(13) 0.0031(13) 0.0112(15) C30 0.0363(18) 0.0323(17) 0.0302(15) 0.0042(13) 0.0037(13) 0.0136(15) C31 0.0332(18) 0.043(2) 0.0396(17) -0.0020(15) 0.0054(14) 0.0167(16) C32 0.0315(18) 0.039(2) 0.0441(18) 0.0006(15) 0.0055(15) 0.0095(15) C33 0.051(2) 0.046(2) 0.0445(19) 0.0125(16) -0.0006(17) 0.0137(18) C34 0.0407(19) 0.0378(19) 0.0365(17) 0.0011(14) 0.0022(15) 0.0101(16) C35 0.069(3) 0.064(3) 0.0349(18) 0.0000(17) -0.0041(18) 0.035(2) C36 0.049(2) 0.050(2) 0.059(2) -0.0058(18) 0.0026(19) 0.0002(19) C25 0.0255(15) 0.0242(16) 0.0416(17) 0.0007(13) -0.0019(13) 0.0091(13) N1 0.0296(14) 0.0330(15) 0.0354(14) 0.0078(12) 0.0032(12) 0.0092(12) N2 0.0513(18) 0.0277(15) 0.0420(16) 0.0022(12) 0.0106(14) 0.0115(14) N3 0.0419(17) 0.0376(17) 0.0424(15) 0.0066(13) 0.0073(13) 0.0186(14) N4 0.0397(16) 0.0292(15) 0.0393(15) 0.0061(12) -0.0029(13) 0.0105(13) O1 0.0273(11) 0.0314(12) 0.0328(10) -0.0028(9) -0.0047(9) 0.0142(9) O2 0.0342(12) 0.0366(13) 0.0450(12) 0.0018(10) -0.0066(10) 0.0199(11) O3 0.0367(13) 0.0438(14) 0.0443(13) 0.0040(10) 0.0111(11) 0.0176(11) O4 0.0620(17) 0.0442(15) 0.0429(13) 0.0163(11) 0.0098(12) 0.0254(13) O5 0.110(3) 0.0423(16) 0.0560(16) 0.0085(13) 0.0181(16) 0.0419(17) O6 0.088(2) 0.0488(16) 0.0363(13) 0.0008(11) 0.0136(13) 0.0242(15) O7 0.0348(12) 0.0250(11) 0.0368(11) 0.0063(9) -0.0036(10) 0.0063(10) O8 0.0424(14) 0.0243(12) 0.0500(13) 0.0029(10) -0.0062(11) 0.0035(11) O9 0.0434(15) 0.0509(16) 0.0582(15) 0.0143(13) 0.0208(13) 0.0159(13) O10 0.102(2) 0.0357(15) 0.0464(14) -0.0028(12) 0.0168(15) 0.0239(15) O11 0.0444(14) 0.0423(14) 0.0456(14) 0.0135(11) 0.0104(12) 0.0138(12) O12 0.112(2) 0.0353(15) 0.0509(15) 0.0090(12) 0.0122(16) 0.0376(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.200(3) . ? C1 O1 1.334(3) . ? C1 C2 1.500(4) . ? C2 C7 1.391(4) . ? C2 C3 1.395(4) . ? C3 C4 1.382(4) . ? C3 N1 1.473(4) . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.380(4) . ? C5 N2 1.475(4) . ? C6 C7 1.391(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 O1 1.455(3) . ? C8 C9 1.524(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C14 1.505(4) . ? C9 C10 1.509(4) . ? C9 C15 1.543(4) . ? C10 C11 1.318(4) . ? C10 H10 0.9500 . ? C11 C12 1.498(4) . ? C11 H11 0.9500 . ? C12 C13 1.503(4) . ? C12 C16 1.546(4) . ? C12 H12 1.0000 . ? C13 C14 1.320(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.518(5) . ? C16 C18 1.533(5) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 O8 1.208(4) . ? C19 O7 1.325(3) . ? C19 C20 1.504(4) . ? C20 C25 1.371(4) . ? C20 C21 1.397(4) . ? C21 C22 1.382(4) . ? C21 N3 1.471(4) . ? C22 C23 1.385(4) . ? C22 H22 0.9500 . ? C23 C24 1.373(4) . ? C23 N4 1.480(4) . ? C24 C25 1.387(4) . ? C24 H24 0.9500 . ? C26 O7 1.460(3) . ? C26 C27 1.533(4) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C32 1.492(4) . ? C27 C28 1.510(4) . ? C27 C33 1.540(4) . ? C28 C29 1.325(4) . ? C28 H28 0.9500 . ? C29 C30 1.501(4) . ? C29 H29 0.9500 . ? C30 C31 1.500(4) . ? C30 C34 1.546(4) . ? C30 H30 1.0000 . ? C31 C32 1.325(5) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 C35 1.524(5) . ? C34 C36 1.528(5) . ? C34 H34 1.0000 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C25 H25 0.9500 . ? N1 O4 1.221(3) . ? N1 O3 1.229(3) . ? N2 O6 1.210(3) . ? N2 O5 1.229(4) . ? N3 O9 1.220(3) . ? N3 O10 1.223(4) . ? N4 O11 1.214(3) . ? N4 O12 1.225(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 126.0(3) . . ? O2 C1 C2 124.2(3) . . ? O1 C1 C2 109.8(2) . . ? C7 C2 C3 118.1(3) . . ? C7 C2 C1 118.6(3) . . ? C3 C2 C1 123.0(3) . . ? C4 C3 C2 122.9(3) . . ? C4 C3 N1 117.4(3) . . ? C2 C3 N1 119.6(3) . . ? C5 C4 C3 116.1(3) . . ? C5 C4 H4 121.9 . . ? C3 C4 H4 121.9 . . ? C6 C5 C4 123.9(3) . . ? C6 C5 N2 117.7(3) . . ? C4 C5 N2 118.4(3) . . ? C5 C6 C7 117.9(3) . . ? C5 C6 H6 121.0 . . ? C7 C6 H6 121.0 . . ? C6 C7 C2 120.8(3) . . ? C6 C7 H7 119.6 . . ? C2 C7 H7 119.6 . . ? O1 C8 C9 107.9(2) . . ? O1 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? O1 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? C14 C9 C10 110.4(2) . . ? C14 C9 C8 110.9(2) . . ? C10 C9 C8 110.1(2) . . ? C14 C9 C15 109.0(3) . . ? C10 C9 C15 110.3(2) . . ? C8 C9 C15 106.0(2) . . ? C11 C10 C9 124.3(3) . . ? C11 C10 H10 117.8 . . ? C9 C10 H10 117.8 . . ? C10 C11 C12 125.2(3) . . ? C10 C11 H11 117.4 . . ? C12 C11 H11 117.4 . . ? C11 C12 C13 110.2(3) . . ? C11 C12 C16 113.1(2) . . ? C13 C12 C16 112.1(3) . . ? C11 C12 H12 107.0 . . ? C13 C12 H12 107.0 . . ? C16 C12 H12 107.0 . . ? C14 C13 C12 125.0(3) . . ? C14 C13 H13 117.5 . . ? C12 C13 H13 117.5 . . ? C13 C14 C9 124.5(3) . . ? C13 C14 H14 117.7 . . ? C9 C14 H14 117.7 . . ? C9 C15 H15A 109.5 . . ? C9 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C9 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C18 111.4(3) . . ? C17 C16 C12 112.5(3) . . ? C18 C16 C12 111.3(3) . . ? C17 C16 H16 107.1 . . ? C18 C16 H16 107.1 . . ? C12 C16 H16 107.1 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O8 C19 O7 125.7(3) . . ? O8 C19 C20 124.0(3) . . ? O7 C19 C20 110.2(2) . . ? C25 C20 C21 118.7(3) . . ? C25 C20 C19 118.6(3) . . ? C21 C20 C19 122.4(3) . . ? C22 C21 C20 122.4(3) . . ? C22 C21 N3 117.4(3) . . ? C20 C21 N3 120.1(3) . . ? C21 C22 C23 116.1(3) . . ? C21 C22 H22 121.9 . . ? C23 C22 H22 121.9 . . ? C24 C23 C22 123.7(3) . . ? C24 C23 N4 118.4(3) . . ? C22 C23 N4 117.9(3) . . ? C23 C24 C25 118.0(3) . . ? C23 C24 H24 121.0 . . ? C25 C24 H24 121.0 . . ? O7 C26 C27 106.8(2) . . ? O7 C26 H26A 110.4 . . ? C27 C26 H26A 110.4 . . ? O7 C26 H26B 110.4 . . ? C27 C26 H26B 110.4 . . ? H26A C26 H26B 108.6 . . ? C32 C27 C28 110.8(3) . . ? C32 C27 C26 110.0(3) . . ? C28 C27 C26 109.1(3) . . ? C32 C27 C33 111.1(3) . . ? C28 C27 C33 109.5(3) . . ? C26 C27 C33 106.3(3) . . ? C29 C28 C27 124.3(3) . . ? C29 C28 H28 117.9 . . ? C27 C28 H28 117.9 . . ? C28 C29 C30 124.5(3) . . ? C28 C29 H29 117.8 . . ? C30 C29 H29 117.8 . . ? C31 C30 C29 111.1(3) . . ? C31 C30 C34 111.7(3) . . ? C29 C30 C34 112.1(3) . . ? C31 C30 H30 107.2 . . ? C29 C30 H30 107.2 . . ? C34 C30 H30 107.2 . . ? C32 C31 C30 124.3(3) . . ? C32 C31 H31 117.9 . . ? C30 C31 H31 117.9 . . ? C31 C32 C27 125.0(3) . . ? C31 C32 H32 117.5 . . ? C27 C32 H32 117.5 . . ? C27 C33 H33A 109.5 . . ? C27 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C27 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 C36 110.9(3) . . ? C35 C34 C30 111.2(3) . . ? C36 C34 C30 111.1(3) . . ? C35 C34 H34 107.8 . . ? C36 C34 H34 107.8 . . ? C30 C34 H34 107.8 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C34 C36 H36A 109.5 . . ? C34 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C34 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C20 C25 C24 121.1(3) . . ? C20 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? O4 N1 O3 124.3(3) . . ? O4 N1 C3 118.2(2) . . ? O3 N1 C3 117.5(2) . . ? O6 N2 O5 124.3(3) . . ? O6 N2 C5 118.8(3) . . ? O5 N2 C5 116.8(3) . . ? O9 N3 O10 124.4(3) . . ? O9 N3 C21 117.6(3) . . ? O10 N3 C21 117.9(3) . . ? O11 N4 O12 124.7(3) . . ? O11 N4 C23 118.1(3) . . ? O12 N4 C23 117.2(3) . . ? C1 O1 C8 116.0(2) . . ? C19 O7 C26 116.6(2) . . ? _diffrn_measured_fraction_theta_max 0.864 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.864 _refine_diff_density_max 0.353 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.054